I thought by now with the new version this issue would be solved. You really should look into
the email handler and get it to work.
Now i had to buy an additional mobileme account just to get this working.

Other programs which send out emails don't care about the settings you describe in your faq and so on.
If i add a smtp server it sends out emails regardless what email address i sent from or which name it has.
It only uses the smtp service.

Then the SMS issue : i have a AQL account and i don't want to use clickatell. I do have the possibility to send an email to sms but the system won't allow me to. It works when i send an email from mobileme to my number. But not in simon. I have solved this by putting a rule in mobileme which forwards the monitoring email to sms but it is far from ideal.

Yes, email is frustrating, and Simon's email support is in need of improvement. I have plans to replace the email engine in Simon with a more modern third-party framework, but I haven't gotten around to that yet. Perhaps in version 3.1?

I've gone a few rounds with the email thing too - When David puts a new engine in there may be more going on, but I've gotten sufficient functions for my purposes for the time being by -
- simon tweeting to it's own twitter account, which is emailed to my mac.com email
- simon tweeting direct to my iphone
- using smtp.mac.com to email my mac.com address

Actually I configured all three for most of my tests as a way of evaluating their consistancy and in the last month or so I'd say all three methods worked every time.